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I used to dress up as a girl since I was 6, with my mom's clothes. I used to stick her tampons up my ass, then, too!Quote:
Originally Posted by Shelby57
Once I hit puberty, I was masturbating with something up my ass, or in my mouth, pretty much all the time.
I was maybe 32 and had a gf who had a voracious appetite for sex. This was back in the day of the first mini super 8 cams, and we’d film ourselves in every position imaginable - she introduced me to 69 rimming, she in me and me in her. I traveled a lot for work and she fake complained that if I was going t be gone so much she’d need either a dildo or another cock while I was away. I returned with a nice, basic battery operated vibrator, which we then used on each other. It wasn’t long before she slipped it onto my asshole as she sucked my cock. It would be another 20 years before I had a guy suck my cock while he teased my ass.
Still waiting to feel the the real Thing!
When I was about 12 or 13 I had a baseball bat pen which I would insert in my ass while I masturbated. A few years later I discovered metal cigar tubes. I have also used a carrot and a banana. Lately I have been fucking myself with a stick of pepperoni.
It would have to be my early teens. Objects would range from toy rockets, markers and hot dogs. Today I have a great big blue dildo feels amazing
Around 11 or 12 I began sticking my middle finger up my ass when I jerked off. I'd suck on it to get it wet then stick it in. Sometimes I'd pull it out, smell it, suck it and stick it back in (still do from time to time). As an adult, I've used anal beads, a butt plug, screwdriver handle, neck of a beer bottle, carrots, and a dildo (too big, makes me bleed). One guy tried to fuck me but I was too tight (nervous, not ready for it) so he gave up and we went back to blowing each other.
I was 4 or 5 when my cousin a neighbor girl and I played games in the barn... we never fucked but we all sucked and I had all our fingers in me as did he and she.
I was late to this game. I was in my late 30’s and started experimenting with playing with my ass. I had an electric toothbrush that had a large handle and vibrated a lot when it was on. I put some lube on it and put it in my ass and then jerked off with it deep in my asshole. I’ve been working my way up to trying a cock ever since. Haven’t done it yet.
I found I enjoyed it quite young but the want to keep stretching it bigger or to see how big an object I could make fit consumed me. Once I found a dildo I couldn’t take I would obsess until my man pussy would take it... depth has never really been what got me. And unfortunately I don’t have my big dick secret hookup... so now use a dildo when I can hide
I was 22 and it was a shemale .......she put the tip her cock in my ass and I got up and ran to the bathroom because I felt I had to go
that is as far as I got
My Mother used to give me enemas. All she wrote. I stopped squirming after awhile. Felt so much better afterwards.
13 for me
I was 25. I went to an Adult Book Store and bought a penis shaped rubber dildo. It was about six inches long and made out of a hard rubber with a set of balls at the suction cup base. It was a while before I allowed myself to be fucked by a man and I found that could be far more pleasurable than using my dildo.
The first thing I put in my ass was one of my fingers and then one of my Mom's brush handle not sure of my age maybe 14 or 15. By 18 I had used a broom handle, beer bottle and I tried one of those yellow wiffle ball bats, the bat was too big at first but I eventually got it in. During my 1st marriage I used a plastic banana. I would eventually get a 8" dildo. It's been 20 odd years since I've put anything in my ass, I really need to get another dildo to play with.
After sucking my first cock about three years ago. I was so amazed about cock and craving the little round ass fucked. I have a smaller tight ass and it was impossible to get a smaller toy inside me. I did it with trying to relax and lubed and pushing constant pressure on my little hole for like 15 minutes straight. It finally slid in and felt so full and ready to cum. My little ass was throbbing and pulsing inside. Still to this day it takes a few minutes of pushing to get the head of my vibrating pulsing cock in me. I so need to find the real thing and let them try.
At 13 or 14 me and a buddy started messing around and he said he was going to just rub his cock in my ass crack which he did for a minute then next thing I know I’m being fucked ! I was shocked but didn’t tell him to stop … I went home with his cum oozing out my no longer virgin ass and yes it wasn’t the last time
I was in my late 20s. It was one of those little souvenir baseball bats. I did kind of like it but it was more of an experiment than anything. Fast forward to my 50s, my wife was on the road for work a lot and I got back into it and felt great. My favorite was a toilet plunger handle covered with a sock held in place by a rubber band and then covered with a condom......hard but soft. Used my feet to work it in and out. I also had I nice 7 inch dildo. I found that I could handle length much better than girth.
18
It was a penis. Hurt at first, he pulled it out and slid a few fingers in, relaxed me a bit and tried again with his cock.
good times.
I was 14 found my mom's toys used her 7 inch dildo. Sat on the floor in front of a mirror so I could watch it go in.
Way before I could shoot cum, my finger.
I was in my 40s. I was in a hotel on business, having a quiet evening in my room after a dinner out and some wine. I decided to take a warm bath, which I almost never do at home. After a bit of just sitting in the warm water relaxing, I started to leisurely stroke myself. Then, since unlike at home I knew I wasn't going to be interrupted, I started to wonder "what if". I started probing my perineum, and discovered it felt really good. I was relaxed enough that I found I could get a couple of soapy fingers inside me. OMG It was a revelation! After quite some time exploring, I let myself build up to an explosive orgasm with one set of fingers up my ass. I felt so drained I had to let myself relax in the water until it wasn't hot any more. After drying myself off, I stayed naked until it was time to go in the morning. I felt like I was hard all night long, and kept waking up for a little stroke every few hours. Later, I explored myself again with soapy fingers during my morning shower.
It took me a few more years before anyone else put something up there. The first few times I tried bottoming didn't go as easily as I'd expected, largely because it wasn't me doing the inserting and I tensed up too much. Now I'm much better at getting relaxed and letting nice gentlemen fuck me.
Okay, I was about 17 and feeling sexually experimental. Like many young guys, I suppose, I wondered what it would feel like having a cock inside me. I ended up borrowing the revovable wooden handle of my father's coping saw. It was approximately the right size and the righ shape, so I unscrewed it, went into our basement shower, got nice and relaxed, and inserted the thing into my anus. I recall it felt pretty good, so I started strokingh my cock with my right hand and working the handle in and out with my left. Somehow I lost my grip on my improvised dildo and the whole thing slipped into my rectum. I panicked at first, imagining the embarrassment of having my folks take me to the ER. Fortunately, after about 15 minutes, I was able to retreive the thing with my fingers, and vowed never to do that again. again!